Santorini: Private Tailor-Made Tour with Oia, Red Beach & Wine

Summary

White alleys, volcanic cliffs and sunlit wine in Santorini’s timeless villages

You’ll wander Santorini’s whitewashed villages, taste local wine under the sun, stand atop volcanic cliffs near Prophet Elias Monastery, and feel ancient history come alive at Akrotiri. With a private guide handling all transport and timing, you can focus on small moments—like laughter in Megalochori or that hush before sunset in Oia—that make this island linger in your memory.

What’s the experience like?

“Don’t rush the wine — it needs the sun as much as we do,” our driver Nikos grinned, passing me a glass at Santo Wines. I’d already lost track of how many colors I’d seen since morning: the blue domes in Oia, the red cliffs above Red Beach, even the black sand at Perivolos that got everywhere (I’m still finding it in my shoes). We started early from Fira — hotel pickup was easy — and Nikos asked what we wanted most. My partner blurted out “history!” so he steered us toward Akrotiri first. Walking through those silent ruins, with dust motes drifting in shafts of light, I felt oddly connected to people who lived here centuries ago. The air smelled faintly of stone and something sweet — maybe wild thyme?

Megalochori was next, and honestly, I wouldn’t have found it on my own. An old woman waved from her doorstep as we wandered narrow lanes; she called out something that made Nikos laugh but wouldn’t translate for us (he said it was better left a mystery). The church bells rang midday and echoed around the square. By then the sun was high and everything felt slow — except for a stray cat chasing shadows across the stones. We cooled off with cold water from Nikos’ car before heading up to Prophet Elias Monastery. The wind up there whipped at our faces and the view stretched forever; I tried to take a photo but gave up because no picture could really catch that feeling.

We ended by dipping our toes in at Red Beach — you have to walk a bit over loose rocks, so bring sandals if you’re clumsy like me — and then finally Oia for those famous sunset colors. It was busy but not overwhelming; everyone just sort of paused together when the sky turned pinkish-orange. Someone nearby started humming quietly (maybe Greek? I couldn’t tell), and for a moment it felt like the whole island was holding its breath. I didn’t expect to feel so… peaceful? Anyway, we were dropped off right at our door after dark, sandy and tired but kind of glowing inside.

Step-by-step itinerary

Day 1 — Explore Santorini's iconic sights

• Visit Oia village and caldera views
• See the Three Bells of Fira
• Explore Megalochori village
• Visit Pyrgos village and Venetian castle
• Relax at Perivolos black-sand beach
• Visit Red Beach cliffs
• See Akrotiri Lighthouse views
• Visit Prophet Elias Monastery
• Explore Akrotiri Archaeological Site
• Discover windmills of Emporio
• Explore Emporio Castelli village
• Enjoy wine tasting at Santo Wines

Top questions

How long is the Santorini private tailor-made tour?

You can choose between 3 to 8 hours; your itinerary depends on your selected duration.

Does this tour include pickup from my hotel or cruise port?

Yes, private pickup and drop-off are included for hotels, ports, or even the airport.

Can I visit both Oia and Akrotiri on one day trip?

Yes, if your chosen tour duration allows enough time for both stops plus travel between them.

Is entrance to Akrotiri Archaeological Site included?

No, entrance tickets and guided tours inside Akrotiri must be purchased separately onsite.

Are there options for wine tasting during this Santorini tour?

Yes, Santo Wines winery can be added to your itinerary if you wish.

Is there much walking involved on this private tour?

Some sites require walking on uneven paths or stairs; moderate fitness is recommended but alternatives can be arranged.

Can families with children join this day trip?

Yes; infant seats are available upon request and most travelers can participate comfortably.

What’s included

Your day includes private transportation around Santorini with an English-speaking local guide who handles all fees and taxes along the way. Bottled water is provided throughout, plus convenient pickup and drop-off at your hotel or cruise port—so you don’t have to worry about logistics or getting back after sunset.